iTunes - confusing to sync with iPhone

Are any of you having trouble figuring out exactly how to sync your music from iTunes into your iPhone, and what all of the available syncing options mean? I have tried every scenario in the sync menu, none of which give me the results that I am looking for. I even called Apple concerning this, and they said that although they understood my frustration, that that is just how it is.

In the sync menu, there are only 2 pertaining tabs: summary and music.
In the summary tab, you have the option to syn only checked songs and videos or to manually manage music and videos.
- I'll start with the option to "manually manage music and videos" from the first tab (summary tab). What exactly does this mean - manually? To me, manually managing music would be to select the songs that you want to sync, but that is available as a second option in this tab - to "sync only checked songs". And if you pick this "manual" option, then you loose the option to "sync music" from the music tab. So - what does this mean? Also, if you deselect this option while your iPhone is connected, you get a message that says "Are you sure that you do not want to manually manage music and videos on your iPhone? All existing content on the iPhone will be replaced with content from your iTunes library"??? What exactly does that mean - that if I deselect, then everything will be removed from my phone and replaced with all songs that I have in iTunes - including apps, contacts, photos, etc.??? Makes no sense whatsoever. I would have to play around with this for a week before figuring this out completely because every time I pick a different option to see what it does, I have to wait for the whole syncing process again. So at this point, I'm not going to worry about that option (although it's aggravating that I cannot figure it out), and instead move on to the "sync only checked songs option".
- So I select to sync only songs that are checked, then I go through all of my lists (main list, purchased list, playlists, etc) and check all of the songs that I want. Simple, right - no, because now you have an additional option under the music tab to "sync music". If you do not select "sync music" from the music tab, instead assuming that your first choice to "sync only checked songs" from the summary tab is sufficient, then you are wrong. You will get 0 songs synced with this option - even though you have selected to sync all checked songs. So why is the option to sync only checked songs even there - to confuse you? So now it is safe to assume that you must select the option to sync music in the music tab (I have tried this option with "sync only checked songs" both selected and unselected from the summary tab - not difference that I can tell. Now your options are to select songs via playlists, genre, and artists. I would think that most people would only use the playlist option since the other options will only work if your entire library is updated with genre, etc. So this means that now you have to create a playlists which together, will contain every song from your library that you want. Why isn't the option to simply sync only checked songs available in the section? Why must your songs be in a category of playlist, genre, artist, etc. in order to sync it? What if you select all of your options here, but you also want songs from you main list that are not contained in a playlist - well, you just will not get that song. And again, why is the option to sync only checked songs available in the summary tab - is it so that you can sync other checked songs from you main list that are not contained in playlists, etc - the answer is no - I synced the phone with "sync music" checked in the music tab, and did not choose the option to sync only checked songs from the summary tab - then I checked some random songs from my main list that were not included in playlists, and synced again - my phone was not updated with the extra random songs from my main list. So this means that, if you check "sync music" from the music tab, then indeed, the option to "sync only checked music" from the summary tab is useless.

There are many, many other weird things that I have discovered while trying to figure this out, but I would have to write a book to describe them. So for me, I only have 3 options to sync music from iTunes: sync the entire library (but then I have to put my girlfriends music on my phone - like Dave Mathews - so this in not the option for me), put all of the songs that I want synced into a playlist (so that sync music option in the music tab will work), or just click and drag the songs that I want to my iphone icon.

I am new to Mac - as a matter of fact, I am waiting on my first Macbook Pro to come in the mail. Often times when I'm reading online about the operation procedures of the Mac and Mac software, it explains that once you learn 1 piece of Mac software, then it's very easy to learn other types of software because they are designed in a similar way - then it says "such as iTunes" - probably because that's that 1 application from Mac that most PC users are familiar with. Well, if all Mac software is as based on a similar funtionality as iTunes, then I am in trouble. ITunes is a great to house your music library, but in terms of usability for syncing, it is the most confusing, misleading program that I have ever used. Instead of offering syncing options under several tabs that contradict each other, make 3 simple choices: sync complete library, syn only checked songs, and sync selected playlists (but with the added option to still sync checked songs from your main list that are not included in playlists).

monkeywhistle, as a person who deals with PC's on every level you can imagine (think CSI) than trust me, a recent switcher, iTunes is the only Apple Software that makes as much sense as mud sometimes. Do not base apple software, hardware or anything else base solely on iTunes.

I'm sure some of the regulars here would differ with my opinion, however, after reading your post, I have to admit, I am having the same issue. I can recommend a piece of software that will help in your sync process. You can find it here, it is called supersync.

I don't have the iPhone, but have the iPod Touch - basically the same thing without the phone. Have not had a problem with iTunes sync. In fact, it syncs up far faster and easier than it does with my regular iPod (though my iPod is a 3rd gen. - they are now much improved).

Maybe I have ADD, but I'm not about to read the original post up there. I think I got about two sentences in before my eyes started crossing.

I am sorry the OP is having difficulty with iTunes syncing. I can only offer that on the first "tab" of iPhone syching is an option to (one time only) force sync from one direction to another, essentially allowing one to "start fresh" without losing data. I hope that will help them. Apart from that, I'm not having any issues with syncing iPhone data to my computer.

For music and video I use the playlist(s) option. Create a playlist, or multiple playlists, drag the content you want into those playlists and sync to them.

Unfortunately there's no playlist concept for apps so if you have multiple iphones/ipod touches connected to the same library you just have to tick/untick the apps you want. But using the playlist concept for music is easy.

I agree with you and others that iTunes is pretty awful in comparison to most Apple software (it's not up there with iPhoto but that's a whole other post ).

iTunes has grown and changed over the years needing to adapt from just music to handling contacts, photo sync, apps, video etc. It doesn't have a single purpose like the rest of the core Apple apps and as such is a bit jumbled.

I think you'll find that once you get organised with playlists you'll be fine.

External hard disk acquisition addict - but admitting the problem is the first step to a robust backupPlease use the reputation system if you think you've been helped - top right of this post

I read the long post and agree 100%. The syncing in iTunes is the worst most un-user friendly program I have ever used. (And I have worked in the I.T. field for years.) I have lost tons of time, music, apps ....trying to use it.

For me to sync is simple, if I have songs A B C on my PC and songs D E F on my iPod, when I sync I want A B C D E F on both devices. The End. How hard can that be?

For music I have found that manually managing it is the most safe way. You just drag over what you want from iTunes to your devices and highlight what you don't want on your device and delete it. I'm not sure that Apps and other stuff works as easily manually. I have not explored those as much.

I love Mac but I hate iTunes. With so many people complaining you think Mac would listen to their customers and get it right.

For me to sync is simple, if I have songs A B C on my PC and songs D E F on my iPod, when I sync I want A B C D E F on both devices. The End. How hard can that be?

The problem with that is that that's not how it's supposed to work AT ALL. iTunes should have songs ABCDEF, and the iPod should have as much of that as it is capable of holding. These are not two separate libraries, they are the same library.

When you run the program the way it is supposed to be run, syncing is not an issue.

When you run the program the way it is supposed to be run, syncing is not an issue.[/QUOTE]"

Most of my problems recently have been with iPad (not Pod) where you can have the 'same' library but different content because you can download independent of your PC. This probably applies to an iPod with WiFi as well.

Where I went wrong initially (and I believe a lot of people do the same) is with the Sync tick option in iTunes. Particularly with the earlier versions. If you removed the tick from a sync option (music,apps,photos...) it basically tells iTunes to delete everything from your device. There were no warnings! (I believe the new version does have a warning.) This happened when I started with the Sync option ticked and I decided to try manual and see how it worked. Opps..too late. But it was resolved by re-syncing which of course can takes ages depending on the size of your library.

I think the point people want to make here is iTunes is not very user friendly especially for those who are not very techy or new to iTunes. It could do with a clear and concise tutorial/manual explaining the options and how they work. Even the tutorial that it presently has assumes that you already understand what syncing is.

To tick or not to tick, that is the question. Or is it tick with sync or tick with manual or no tick. I'm ticked!

I think the point people want to make here is iTunes is not very user friendly especially for those who are not very techy or new to iTunes. It could do with a clear and concise tutorial/manual explaining the options and how they work. Even the tutorial that it presently has assumes that you already understand what syncing is.

I think that's a reasonable statement; although anecdotally I haven't run into many people who have that particular issue, I have seen the "double entries" issue a time or two and agree that Apple could make syncing more elegant and provide more info for troubleshooting, certainly.

What I've found happens a lot is that people think that if the music is on their iPod they can then delete it from iTunes, which is incorrect. I'm sure there are ways to make that work, but that's not the way the program is meant to be used.

OP,
Manually managing Music and Videos, you can just click on the file you want and drag it to your iPhone. You don't have to use the tab at the top.
You see a song in the list: "Yesterday by the Beatles" Normally, you'd double click it to play it. Instead, click and hold, then drag it to the left where you see your iPhone in the list. It will then transfer to your phone.

To get something that you downloaded over the air off your iPhone back into iTunes, on the left where your iPhone appears in iTunes, make sure the little triangle next to iPhone is pointing down and you can see the sub folders (Music, Movies, Playlists Purchased, etc) look for Purchased CMD+click and pick transfer purchases.

I just tried to sync the music on my phone, but because iTunes isn't clear (and this is an understatement), I don't know what the options mean. I'm afraid that I'm going to delete things that I still need, so I didn't do it.

The iTunes system is poorly designed. It is by far the worst feature that Apple has, and is one of the worst interfaces OF ANY KIND that I have ever run across. This is pretty ironic, considering what Apple has built it's reputation on.

I've got my iPhone and my MacBook and love the stuff they do, but Windows 7 blows this out of the water when it comes to manipulating files.

I'm VERY techy and I'm not new to iTunes. It's poor design, plain and simple. The problem with Apple is that they won't change things that don't work. I feel that they think they're good at everything, when they're not.

Whew, what a post! I could barely get through it because it sounds like monkeywhistle is making it way more complicated than it needs to be. I think your first mistake was getting thrown by the Summary tab's Options list that has "Manually manage music and videos". I would just ignore that and leave it unchecked. I know this option seems like it gives you more control, but it's really a pain compared to just having it automatically sync all changes made to playlists, library, etc.

For instance, let's say you just added ten new songs to your library and deleted five. If you DON'T opt to manually manage music, iTunes will automatically sync the ten new songs to your device and delete the five missing ones without any action on your part. With the manually manage option checked, you'd have to drag the ten new songs to the device or they won't get synced, and you have to manually remove the five deleted songs.

I would just leave manual managing off and simply choose which playlists, albums, etc you want to sync. It's really not that hard at all. Though I think some of these options could be better explained within the interface.